CN102292324A - Novel cycloalkene derivatives and organic electronic devices using the same - Google Patents

Novel cycloalkene derivatives and organic electronic devices using the same Download PDF

Info

Publication number
CN102292324A
CN102292324A CN2010800050814A CN201080005081A CN102292324A CN 102292324 A CN102292324 A CN 102292324A CN 2010800050814 A CN2010800050814 A CN 2010800050814A CN 201080005081 A CN201080005081 A CN 201080005081A CN 102292324 A CN102292324 A CN 102292324A
Authority
CN
China
Prior art keywords
group
unsubstituted
compound
formula
aromatic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN2010800050814A
Other languages
Chinese (zh)
Other versions
CN102292324B (en
Inventor
张惠荣
李载澈
裵在顺
金正坤
金性昭
金昌焕
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Corp
Original Assignee
LG Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LG Chemical Co Ltd filed Critical LG Chemical Co Ltd
Publication of CN102292324A publication Critical patent/CN102292324A/en
Application granted granted Critical
Publication of CN102292324B publication Critical patent/CN102292324B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Thin Film Transistor (AREA)
  • Photovoltaic Devices (AREA)

Abstract

The present invention relates to a novel cycloalkene derivative and an organic electronic device using the same. The cycloalkene derivative according to the present invention functions as a hole-injection, hole-transport, electron-injection, electron-transport, or light-emitting material, and especially, independently functions as a light-emitting host or dopant, in an organic electronic device such as an organic light-emitting device.

Description

New cycloalkene derivative and use its organic electronic devices
Technical field
The present invention relates to new cycloalkene derivative and use its organic electronic devices.The application requires the right of priority of on January 20th, 2009 to the korean patent application No.10-2009-0004600 of KIPO submission, and whole disclosures of this application are included this paper by reference in.
Background technology
Organic electronic devices is meant the device that need utilize hole and/or electronics exchange charge between electrode and organic materials.Described organic electronic devices is broadly divided into following two classes according to principle of work.First, have a kind of electron device, wherein form a kind of exciton (exiton) by the photon that flows to this device from external light source a kind of organic material layer, described exciton is divided into electronics and hole, described electronics moves to different electrodes respectively with the hole, and as current source (voltage source).The second, there is a kind of electron device, wherein, hole and/or electronics form in the organic materials semi-conductor at interface by being injected into respect to electrode, and described device is by injected electrons and hole operation.
Examples of organic electronic is Organic Light Emitting Diode, organic solar batteries, organic photoconductor (OPC), organic transistor etc., these devices need hole injection or transport material, electronics injection or transport material or luminescent material, to drive described device.
Hereinafter, will mainly describe Organic Light Emitting Diode in detail.But in described organic electronic devices, hole injection or transport material, electronics injection or transport material or luminescent material move based on similarity principle.
Generally speaking, the organic light emission phenomenon is meant a kind of by using organic materials electric energy to be changed into the phenomenon of luminous energy.Utilize the Organic Light Emitting Diode of organic light emission phenomenon to have a kind of structure, this structure comprises an anode, a negative electrode and an organic layer that places therebetween usually.Herein, most of organic material layers all have a kind of multilayered structure that comprises differing materials, to increase the efficient and the stability of Organic Light Emitting Diode, can comprise for example hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc.In described organic LED structure, if apply voltage between two electrodes, then the hole is from anode injection organic material layer, electronics is from negative electrode injection organic material layer, when injected holes and electronics meet each other, forms exciton, when this exciton when ground state is landed, just send light.Performances such as that known this Organic Light Emitting Diode has is luminous such as magnetic, high brightness, high-level efficiency, low driving voltage, wide visual angle, high-contrast, the high speed of response.
In described Organic Light Emitting Diode, the material that is used as organic material layer can be divided into luminescent material and charge transfer material according to its function, for example hole-injecting material, hole mobile material, electron transport material, electronics injecting material etc.Described luminescent material can be divided into polymer and low molecule-type according to molecular weight, the phosphorescent material that can divide for fluorescent material that the singlet excited by electric field obtains and be obtained by the triplet excited state of electric field according to luminous mechanism.In addition, described luminescent material can be divided into blueness, green and red illuminating material and yellow and orange luminescence material for realizing that better Natural color designs according to glow color.
Simultaneously, under the situation of only using a kind of material as luminescent material,, maximum emission wavelength is moved to long wave, and can reduce colour purity or owing to the decay of luminescence effect reduces diode efficient by the interaction between the molecule.Therefore, increase colour purity and increase luminous efficiency, can use matrix/doping agent system as luminescent material for shifting by energy.Principle is, if a small amount of band-gap energy is mixed with described luminescent layer than the low doping agent of matrix that forms luminescent layer, then by the exciton transfer of luminescent layer generation to doping agent, thereby with high efficiency light-emitting.In the case, because the wavelength of matrix moves to the wavelength bandwidth of doping agent, so can obtain required optical wavelength according to the kind of used doping agent.
For making Organic Light Emitting Diode fully demonstrate above-mentioned premium properties, constitute the material of organic material layer (for example hole-injecting material, hole mobile material, luminescent material, electron transport material, electronics injecting material etc.) in the diode, should take on by stable and effective material.But, the stable and effective organic materials layer material that is used for Organic Light Emitting Diode is not developed as yet.Therefore, need a kind of new material of exploitation, and even above-mentioned other organic electronic devicess are also had similarly necessity of exploitation novel material.
Summary of the invention
Technical problem
Made great efforts to make the present invention so that a kind of new stable and effective cycloalkene derivative and a kind of organic electronic devices that uses it to be provided.
Technical scheme
An exemplary of the present invention provides a kind of compound by following formula 1 expression.
[formula 1]
Figure BPA00001406840200031
Wherein
R 1Be one by-[Ar] mThe substituting group group that-X represents,
P is an integer among the 0-3, and l is an integer among the 1-4, and m is an integer among the 0-5,
Ar is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S arylene group or a replacement or unsubstituted 2-C 50Divalent heterocyclic group,
Ar ' is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group,
X is a substituting group group that is selected from following structural formula,
Figure BPA00001406840200032
In the said structure formula, Cy is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group,
R 2Be selected from: C replacement or unsubstituted 1-C 40Alkyl group; That replace or unsubstituted C 1-C 40Alkoxy base; That replace or unsubstituted C 2-C 40Alkenyl group; That replace or unsubstituted C 6-C 50Aromatic yl group; That replace or unsubstituted C 6-C 50The arylamines group; The C that contains N, O or the assorted element of S that replace or unsubstituted 2-C 50The heteroaryl amine groups; The C that contains O, N or the assorted element of S that replace or unsubstituted 2-C 50Heterocyclic group; The amino group that replaces; Nitrile group; Nitryl group; Halogen group; And amine groups,
N is an integer among the 0-5, and o is an integer among the 0-10, and o be 2 or bigger situation under, each R 2Each other can be identical or different, and
L, m or p be 2 or bigger situation under, Ar, Ar ' or R 1Each other can be identical or different.
Another exemplary of the present invention provides a kind of organic electronic devices, it comprises first electrode, second electrode and one or more organic material layer that places between described first electrode and second electrode, and wherein one or more layers in the organic material layer comprises the compound by formula 1 expression.
Beneficial effect
The compound of illustrative embodiments of the invention can be used as hole-injecting material, hole mobile material, electronics injecting material and electron transport material or the luminescent material in Organic Light Emitting Diode and the organic electronic devices, and the organic electronic devices of illustrative embodiments of the invention efficient, driving voltage and stable aspect demonstrate premium properties.
Description of drawings
Fig. 1 is the synoptic diagram of the structure of the Organic Light Emitting Diode of an exemplary of explanation the present invention.
Fig. 2 is for preparing the MS spectrum of the compd A of preparation among the embodiment 1 in the present invention.
Fig. 3 is for preparing the MS spectrum of the compound 2 of preparation among the embodiment 2 in the present invention.
Fig. 4 is for preparing the MS spectrum of the compound 77 of preparation among the embodiment 3 in the present invention.
Fig. 5 is for preparing the MS spectrum of the Compound C of preparation among the embodiment 4 in the present invention.
Fig. 6 is for preparing the MS spectrum of the compound 10 of preparation among the embodiment 5 in the present invention.
Embodiment
Hereinafter, the present invention will be described in more detail.
An exemplary of the present invention relates to the compound of formula 1 expression.
[formula 1]
Figure BPA00001406840200041
Wherein
R 1Serve as reasons-[Ar] mThe substituting group group that-X represents,
P is an integer among the 0-3, and l is an integer among the 1-4, and m is an integer among the 0-5,
Ar is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S arylene group or a replacement or unsubstituted 2-C 50Divalent heterocyclic group,
Ar ' is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group,
X is a substituting group group that is selected from following structural formula,
Figure BPA00001406840200051
In the said structure formula, Cy is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group,
R 2Be selected from: C replacement or unsubstituted 1-C 40Alkyl group; That replace or unsubstituted C 1-C 40Alkoxy base; That replace or unsubstituted C 2-C 40Alkenyl group; That replace or unsubstituted C 6-C 50Aromatic yl group; That replace or unsubstituted C 6-C 50The arylamines group; The C that contains N, O or the assorted element of S that replace or unsubstituted 2-C 50The heteroaryl amine groups; The C that contains O, N or the assorted element of S that replace or unsubstituted 2-C 50Heterocyclic group; The amino group that replaces; Nitrile group; Nitryl group; Halogen group; And amine groups,
N is an integer among the 0-5, and o is an integer among the 0-10, o be 2 or bigger situation under, each R 2Each other can be identical or different, and
L, m or p be 2 or bigger situation under, Ar, Ar ' or R 1Each other can be identical or different.
In this exemplary of the present invention, in formula 1, be that following formula and CY are C at X 6Aryl is under the situation of phenyl ring, and n is preferably 1 or bigger, and more preferably 1 or 2.
In this exemplary of the present invention, in formula 1, be under the situation of following formula at X, preferred R 1Be arranged in 9 of formula 1 anthracene, and at least one Ar ' is positioned at 10 of anthracene.In the case, at least one substituting group group can be positioned at another position of anthracene in addition.
Figure BPA00001406840200053
In this exemplary of the present invention, in formula 1, be under the situation of following formula at X, p is an integer among the 1-3, and Ar ' is preferably a C replacement or unsubstituted 6-C 50The C that contains the assorted element of a N aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group, and a replacement more preferably or unsubstituted C 6-C 50Aromatic yl group.
Figure BPA00001406840200061
In formula 1, more preferably m is 0 or 1.
In formula 1, be that preferred l is 2-4 under 0 the situation at p.
Formula 1 is not being had under the situation about specifying, term " replacement or unsubstituted " is meant by one or more and is selected from following substituting group and replaces or be not substituted: heavy hydrogen, halogen, alkyl, thiazolinyl, alkoxyl group, aryl, arylalkyl, aryl alkenyl, heterocyclic radical, carbazyl, fluorenyl, itrile group and ethynyl, but this term is not limited thereto.
In formula 1, under alkyl, alkoxyl group, thiazolinyl, aryl, arylamines, heteroaryl amine or the substituted situation of heterocyclic group, preferred described group is selected from following substituting group and replaces by one or more: heavy hydrogen, halogen, alkyl, thiazolinyl, replacement or unsubstituted alkoxyl group, replacement or unsubstituted arylamines, replacement or unsubstituted aryl, replacement or unsubstituted arylalkyl, replacement or unsubstituted aryl alkenyl, replacement or unsubstituted heterocyclic, itrile group and replacement or unsubstituted ethynyl.Under the substituted situation of amino group, preferably this group is selected from following substituting group and replaces by one or more: alkyl, thiazolinyl, replacement or unsubstituted aryl, replacement or unsubstituted arylalkyl and replacement or unsubstituted aryl alkenyl.
Formula 1 is not being had under the situation about specifying, and described alkyl and alkoxy base preferably have 1-40 carbon atom, and more preferably 1-20 carbon atom.In addition, described thiazolinyl preferably has 2-40 carbon atom, and more preferably 2-20 carbon atom.In addition, described aryl preferably has 6-40 carbon atom, and more preferably 6-20 carbon atom.In addition, described heterocyclic group preferably has 2-50 carbon atom, more preferably 4-40 carbon atom, more preferably 4-20 carbon atom.In addition, described arylamines group preferably has 6-60 carbon atom, and more preferably 6-24 carbon atom.In addition, described heteroaryl amine groups preferably has 2-60 carbon atom, preferred 4-40 carbon atom, and more preferably 4-20 carbon atom.
Preferably the compound by formula 1 expression is with following formula 2-1 or formula 2-2.
Formula 2-1 formula 2-2
Figure BPA00001406840200071
In formula 2-1 and formula 2-2, R 1Identical with Ar ' with the definition in the formula 1, and at R 1Have under the situation more than 2, can be same to each other or different to each other, and
L is an integer among the 1-3.
In addition, the compound of preferably being represented by formula 1 is with following formula 3-1 or formula 3-2.
Figure BPA00001406840200072
In formula 3-1 and formula 3-2, R 1Identical with Ar ' with the definition in the formula 1, and at R 1Have under the situation more than 2, can be same to each other or different to each other, and
L is an integer among the 0-2.
In addition, be with following formula 4-1 any to the formula 4-4 preferably by the compound of formula 1 expression.
Figure BPA00001406840200073
At formula 4-1 to formula 4-4, each R 1Identical with the definition in the formula 1, and can be same to each other or different to each other, and
Each Ar ' is identical with the definition in the formula 1, and can be same to each other or different to each other.
In addition, be with following formula 5-1 any to the formula 5-3 preferably by the compound of formula 1 expression.
Figure BPA00001406840200081
At formula 5-1 to formula 5-3, each R 1Identical with the definition in the formula 1, and can be same to each other or different to each other, and
Each Ar ' is identical with the definition in the formula 1, and can be same to each other or different to each other.
In addition, be with following formula 6-1 any to the formula 6-4 preferably by the compound of formula 1 expression.
Figure BPA00001406840200082
At formula 6-1 to formula 6-4, each R 1Identical with the definition in the formula 1, and can be same to each other or different to each other, and
Each Ar ' is identical with the definition in the formula 1, and can be same to each other or different to each other.
In addition, be with following formula 7-1 any to the formula 7-4 preferably by the compound of formula 1 expression.
Formula 7-1 formula 7-2
Figure BPA00001406840200091
At formula 7-1 to formula 7-4, each R 1Identical with the definition in the formula 1, and can be same to each other or different to each other, and
Each Ar ' is identical with the definition in the formula 1, and can be same to each other or different to each other.
In addition, be with following formula 8-1 any to the formula 8-5 preferably by the compound of formula 1 expression.
Figure BPA00001406840200092
At formula 8-1 to formula 8-5, each R 1Identical with the definition in the formula 1, and can be same to each other or different to each other, and
Each Ar ' is identical with the definition in the formula 1, and can be same to each other or different to each other.
Above various in, preferred Ar is by C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10Replace or the unsubstituted C of alkyl silyl-group 6-C 26Arylidene; Or by C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 26Divalent heterocyclic group.
In addition, the arylene group among the preferred described Ar is selected from phenylene, naphthylidene, biphenylene, anthrylene and following structural formula.
Figure BPA00001406840200101
Above various in, preferred R 2Be C 1-C 10Alkyl group; Replaced or unsubstituted C by following group 6-C 26Aromatic yl group: C 1-C 10Alkyl, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group; Or replaced by following group or unsubstituted and contain O, N or the heteroatomic C of S 2-C 26Heterocyclic group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group.
Above various in, preferred R 1Be selected from the group of representing by following structural formula, but R 1Be not limited thereto.
Above various in, preferred
Figure BPA00001406840200111
Above various in, Ar ' is preferably by following group and replaces or unsubstituted C 6-C 26Aromatic yl group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group; Or replaced by following group or unsubstituted and contain O, N or the heteroatomic C of S 2-C 26Heterocyclic group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group, Ar ' more preferably is selected from the substituting group group of being represented by following structural formula, but is not limited thereto.
Figure BPA00001406840200121
The specific embodiment of the compound of preferred illustrative embodiments of the invention is selected from following compound 1-88, but is not limited thereto.
Figure BPA00001406840200131
Figure BPA00001406840200141
Figure BPA00001406840200151
Figure BPA00001406840200161
Figure BPA00001406840200171
Figure BPA00001406840200181
The boronic acid compounds that the compound of illustrative embodiments of the invention can be by making anthracene derivant and the halogenide of cycloalkene derivative react each other and prepare.In the case, can use reaction conditions known in the art.For example.The boronic acid compounds of anthracene derivant and the halogenide of cycloalkene derivative can four triphenylphosphines close palladium and potassiumphosphate in the presence of the reaction each other by adding solvent (for example water and THF).
Second aspect of the present invention relates to a kind of organic electronic devices, it comprises first electrode, second electrode, one or more organic material layer that places between described first electrode and second electrode, and wherein one or more layers in the organic material layer comprises above-claimed cpd.
In this article, organic material layer can comprise electronics or hole injection layer and electronics or hole transmission layer, and described electronics or hole injection layer and described electronics or hole transmission layer can comprise above-claimed cpd.
In addition, described organic material layer can comprise luminescent layer, and described luminescent layer can comprise above-claimed cpd.
In the case, preferred described organic electronic devices is selected from Organic Light Emitting Diode, organic solar batteries, organic photoconductor (OPC) and organic transistor.
When the preparation organic electronic devices, the compound of illustrative embodiments of the invention can form an organic material layer by vacuum deposition method and solution coat method.Herein, the illustrative of solution coat method but non-limiting instance comprises spin-coating method, dip coating, ink jet printing method, silk screen print method, spray method and rolling method.
Organic electronic devices of the present invention can use material known in the art and method preparation, and difference is that the one deck at least in the organic material layer comprises compound of the present invention, i.e. formula 1 compound.
The organic material layer of organic electronic devices of the present invention can have a kind of single layer structure, or is laminated with the multilayered structure of two or more organic material layers.For example, the organic electronic devices of illustrative embodiments of the invention can have a kind of like this structure, and this structure comprises hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and the electron injecting layer as organic material layer.But the structure of described organic electronic devices is not limited thereto, and can comprise the organic material layer of lesser number.
In addition, organic electronic devices of the present invention can for example prepare by stacked in succession one first electrode, organic material layer and one second electrode on a kind of substrate.In the case, can use physical vapor deposition (PVD, Physical Vapor Deposition) method, for example sputtering method (sputtering) or electron-beam vapor deposition method (e-beam evaporation), but described method is not limited thereto.
For anode material, general preferred use has high work function (work function) so that successfully the hole is injected into material in the organic material layer.The detailed example of the anode material that can use in the present invention has metal, for example vanadium, chromium, copper, zinc, gold etc., or its alloy; Metal oxide, for example zinc oxide, indium oxide, indium tin oxide (ITO), indium-zinc oxide (IZO) etc.; The composition of metal and oxide compound, for example ZnO:Al or SnO 2: Sb; And conductive polymers, for example poly-(3 methyl thiophene), poly-[3,4-(ethylidene-1,2-dioxy base) thiophene] (PEDT), polypyrrole and polyaniline, but be not limited thereto.
For cathode material, general preferred use has low work function so that smoothly electronics is injected the material of described organic material layer.The detailed example of cathode material has metal, for example magnesium, calcium, sodium, potassium, titanium, indium, iridium, lithium, gadolinium, aluminium, silver, tin and lead, or its alloy; And sandwich, for example LiF/Al or LiO 2/ Al, but be not limited thereto.
Described hole-injecting material is for can under low pressure receiving the material from the anodic hole well, the HOMO of preferred described hole-injecting material (highest occupied molecular orbital, highest occupied molecular orbital) is worth between the HOMO of the work function of anode material and contiguous organic material layer.The detailed example of hole-injecting material has the organic materials of organic materials, six nitriles, six azepine benzophenanthrenes (hexanitrile hexaazatriphenylene) and quinacridone (quniacridone) series of metalloporphyrin (porphyrine), oligothiophene and arylamines series; the organic materials of perylene (perylene) series, with the conductive polymers of anthraquinone, polyaniline and Polythiophene series, but be not limited thereto.
Described hole mobile material is transferred to the material of luminescent layer, the preferred material with big hole mobility that uses for receiving from the hole of anode or hole injection layer and with the hole that receives.Its detailed example has organic materials, the conducting polymer based on arylamines and comprises the block polymer of conjugate moiety and non-conjugated part simultaneously, but is not limited thereto.
Thereby described luminescent material is for receiving respectively from the hole and the electronics of hole transmission layer and electron transfer layer and make their materials in conjunction with the light of visible emitting scope, the preferred material that fluorescence or phosphorescence are had good photon efficiency that uses.Its detailed example has 8-hydroxyl-quinoline aluminum complex compound (Alq 3); Compound based on carbazole; Two polystyrene-based (dimerized styryl) compound; BAlq; 10-hydroxy benzo quinoline-metallic compound; Compound based on benzoxazole, benzothiazole and benzoglyoxaline; Based on poly-(to phenylene vinylidene) polymkeric substance (PPV); Volution (spiro) compound; Poly-fluorenes, lubrene etc., but be not limited thereto.
Described electron transport material is for receiving well from the electronics of negative electrode and with the transfer transport that the receives material to luminescent layer, the material that preferred use has big electronic mobility.Its detailed example has the oxine aluminium complex; Contain Alq 3Complex compound; Organic free radical compound; Flavonol metal complex etc., but be not limited thereto.
Organic Light Emitting Diode of the present invention can be top emission type, bottom-face luminous type or lighting at two sides type according to material therefor
The compounds of this invention in addition can be in organic electronic devices (for example organic solar batteries, organic photoconductor and organic transistor), with the similar principle operation of the principle that is applied to Organic Light Emitting Diode.
Embodiment
Preparation will be described in detail in preparation embodiment and embodiment by the method for the organic electronic devices that this compound is used in the compound and the preparation of formula 1 expression.But, describes described preparation embodiment and embodiment and be for the present invention is described, but scope of the present invention is not limited thereto.
Preparation embodiment
＜preparation embodiment 1〉compd A synthetic
With the tricresyl phosphite phenylester [(PhO) 3P] (18.5mL 70mmol) places 200mL anhydrous methylene chloride and be cooled to-78 ℃.Under nitrogen atmosphere, slowly add bromine (4mL, 77mmol).Thereafter, add Trimethylamine Anhydrous (12mL, 84mmol) and Tetralone an intermediate of Sertraline (tetrarone) (9.36g, 64mmol) and under condition of stirring at 18 hours internal heating to room temperature.Thereafter, by heat about 2 hours, reflux and use chromatography purification, obtain the 12.8g compd A, productive rate is 96%.[M+]＝208
＜preparation embodiment 2〉compound 2 synthetic
Figure BPA00001406840200222
4g compound S 1 (11.4mmol), 2.4g compd A (11.4mmol), 265mg four triphenylphosphines are closed palladium (Pd[PPh 3] 4, 0.229mmol) with 4.87g potassiumphosphate (K 3PO 4, 22.9mmol) place 100mL water and 100ml THF, and reflux and stirring.After 18 hours, temperature is reduced to normal temperature, isolates organic layer.By except that the solid that desolvates and recrystallization produces in chloroform/methanol, obtain 3.08g compound 2, productive rate is 62%.[M+H]＝433
＜preparation embodiment 3〉compound 77 synthetic
Figure BPA00001406840200231
4g compound S 2 (7.2mmol), 1.65g compd A (7.9mmol), 166mg four triphenylphosphines are closed palladium (Pd[PPh 3] 4, 0.143mmol) with 3.04g potassiumphosphate (K 3PO 4, 14.3mmol) place 100mL water and 100ml THF, and reflux and stirring.After 18 hours, temperature is reduced to normal temperature, isolates organic layer.By except that the solid that desolvates and recrystallization produces in chloroform/methanol, obtain 3.6g compound 77, productive rate is 89%.[M+H]＝559
＜preparation embodiment 4〉Compound C synthetic
Below prepare disclosed method enforcement among the open text No.10-2007-0043664 of the patent application of looking into according to Korean unexamined.
Figure BPA00001406840200232
With indenes (indene, 259mmol, 30g) and distilled water (9mL) place methyl-sulphoxide (DMSO, 90mL) in, cool the temperature to 0 ℃, and to wherein slowly add N-bromo-succinimide (NBS, 263mmol, 46.9g).The temperature of this solution is risen to normal temperature, and stirred this solution 12 hours., by distilled water make reaction finish after, use the extracted with diethyl ether organic layer, remove moisture by anhydrous magnesium sulfate thereafter.After the filtration under diminished pressure, by the pressure that reduces filtrate remove desolvate and in hexane recrystallization, obtain compd B (38.9g, 72%).
(p-TsOH, 2.6mmol 0.5g) are dissolved in the 60mL toluene, and stirring heating 24 hours, anhydrate by using the Tin-Stock method to remove simultaneously with 14.3g compd B and tosic acid.By solution temperature being reduced to normal temperature and using fractionating process to obtain Compound C (7.8g, 60%).
[M]+＝194
＜preparation embodiment 5〉compound 10 synthetic
Figure BPA00001406840200241
4g compound S 1 (11.4mmol), 2.69g compd A (13.8mmol), 265mg four triphenylphosphines are closed palladium (Pd[PPh 3] 4, 0.229mmol) with 4.87g potassiumphosphate (K 3PO 4, 22.9mmol) place 100mL water and 100ml THF, and reflux and stir.After 18 hours, temperature is reduced to normal temperature, isolates organic layer.By obtaining 4g compound 10 except that the solid that desolvates and recrystallization generates in chloroform/methanol, productive rate is 84%.[M+H]＝419
Experimental example 1
To scribble thickness is
Figure BPA00001406840200242
The glass substrate of ITO (tin indium oxide, indium tin oxide) film immerse and wherein to be dissolved with in the distilled water of sanitising agent, and use ultrasonic washing.In the case, sanitising agent used herein is the product that is available commercially from Fisher Co., and described distilled water filters twice by the strainer (Filter) that use is available commercially from Millipore Co..ITO washing 30 minutes uses distilled water to repeat 2 ultrasonic washings 10 minutes then.After finishing with distilled water wash,, that products obtained therefrom is dry and be transferred in the plasma body washing machine subsequently by using solvent (for example Virahol, acetone and methyl alcohol) to carry out ultrasonic washing.By using oxygen plasma, then this substrate is transferred in the vacuum deposition machine described substrate washing 5 minutes.
On the ito transparent electrode of preparation thus, deposit by heating under vacuum
Figure BPA00001406840200243
Six nitriles, the six azepine benzophenanthrenes (hexanitrile hexaazatriphenylene) of thickness are to form hole injection layer.Under vacuum state, deposit NPB thereon as hole mobile material
Figure BPA00001406840200244
Afterwards in the vacuum state deposit
Figure BPA00001406840200245
The compound 2 and the doping agent D1 compound as matrix of thickness are as luminescent layer.
Figure BPA00001406840200251
On described luminescent layer, by under vacuum state, on this luminescent layer, depositing
Figure BPA00001406840200252
The E1 of thickness and form that electronics injects and transport layer.On this electronics injection and transport layer, deposit subsequently
Figure BPA00001406840200261
The lithium fluoride of thickness (LiF) and
Figure BPA00001406840200262
The aluminium of thickness, thus negative electrode formed.
Experimental example 2
Implement this test in the mode identical with experimental example 1, difference is that deposited compound 77 replaces compounds 2.
Experimental example 3
Implement this test in the mode identical with experimental example 1, difference is that deposited compound 10 replaces compounds 2.
In above method, the sedimentation velocity of organic substance remains on
Figure BPA00001406840200263
The sedimentation velocity of lithium fluoride remains on
Figure BPA00001406840200264
The sedimentation velocity of aluminium remains on
Figure BPA00001406840200265
Comparing embodiment
Implement this test in the mode identical with experimental example 1, difference is, uses following compound [H1] to replace compound 2.
Figure BPA00001406840200266
The test-results of experimental example and comparing embodiment is described in the following table 1.
Measurement is at 50mA/cm 2Current density under carry out, and the general non-ring olefin material that replaces known cycloolefin is compared and assesses.In general, can see that the compound that contains cycloolefin has similar luminous efficiency and lower voltage characteristic.
[table 1]

Claims (18)

1. compound by following formula 1 expression:
[formula 1]
Figure FPA00001406840100011
Wherein
R 1Be one by-[Ar] mThe substituting group group that-X represents,
P is an integer among the 0-3, and l is an integer among the 1-4, and m is an integer among the 0-5,
Ar is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S arylene group or a replacement or unsubstituted 2-C 50Divalent heterocyclic group,
Ar ' is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group,
X is a substituting group group that is selected from following structural formula,
Figure FPA00001406840100012
In the said structure formula, Cy is a C replacement or unsubstituted 6-C 50The C that contains N, O or the assorted element of a S aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group,
R 2Be selected from: C replacement or unsubstituted 1-C 40Alkyl group; That replace or unsubstituted C 1-C 40Alkoxy base; That replace or unsubstituted C 2-C 40Alkenyl group; That replace or unsubstituted C 6-C 50Aromatic yl group; That replace or unsubstituted C 6-C 50The arylamines group; The C that contains N, O or the assorted element of S that replace or unsubstituted 2-C 50The heteroaryl amine groups; The C that contains O, N or the assorted element of S that replace or unsubstituted 2-C 50Heterocyclic group; The amino group that replaces; Nitrile group; Nitryl group; Halogen group; And amine groups,
N is an integer among the 0-5, and o is an integer among the 0-10, o be 2 or bigger situation under, each R 2Each other can be identical or different, and
L, m or p be 2 or bigger situation under, Ar, Ar ' or R 1Each other can be identical or different.
2. the compound of claim 1, wherein said compound by formula 1 expression is selected from compound 2-1 to 8-5:
Figure FPA00001406840100021
Figure FPA00001406840100031
Figure FPA00001406840100041
Wherein
Each R 1Identical with the definition in the formula 1, and can be same to each other or different to each other,
Each Ar ' is identical with the definition in the formula 1, and can be same to each other or different to each other.
3. the compound of claim 1, wherein Ar be one by C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10Replace or the unsubstituted C of alkyl silyl-group 6-C 26Arylene group; Or one by C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 26Divalent heterocyclic group.
4. the compound of claim 3, wherein said arylene group is selected from phenylene group, naphthylidene group, biphenylene group, anthrylene group and following structural formula:
Figure FPA00001406840100042
5. the compound of claim 1, wherein R 2Be C 1-C 10Alkyl group; Replaced or unsubstituted C by following group 6-C 26Aromatic yl group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group; Or replaced by following group or unsubstituted and contain O, N or the heteroatomic C of S 2-C 26Heterocyclic group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group.
6. the compound of claim 1, wherein m is 0 or 1.
7. the compound of claim 1, wherein R 1Be selected from the substituting group group of representing by following structural formula:
Figure FPA00001406840100051
8. the compound of claim 1, wherein Ar ' is for to be replaced or unsubstituted C by following group 6-C 26Aromatic yl group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group; Or following group replaces or unsubstituted and contain O, N or the heteroatomic C of S 2-C 26Heterocyclic group: C 1-C 10Alkyl group, C 6-C 12Aromatic yl group, by C 6-C 12Aromatic yl group replaces or is unsubstituted and contain O, N or the heteroatomic C of S 2-C 12Heterocyclic group, silyl-group or C 1-C 10The alkyl silyl-group.
9. the compound of claim 8, wherein Ar ' is selected from the substituting group group of being represented by following structural formula:
Figure FPA00001406840100061
10. the compound of claim 1, wherein X is selected from following variously, and CY is C 6Aryl, and n is 1 or bigger:
11. the compound of claim 1, wherein X represents following formula, R 1Be arranged in 9 of formula 1 anthracene, and at least one Ar ' is positioned at 10 of anthracene:
Figure FPA00001406840100063
12. the compound of claim 1, wherein X represents following formula, and p is an integer among the 1-3, and Ar ' is a C replacement or unsubstituted 6-C 50The C that contains the assorted element of a N aromatic yl group or a replacement or unsubstituted 2-C 50Heterocyclic group:
13. the compound of claim 1, wherein said compound by formula 1 expression is selected from following compound 1-88:
Figure FPA00001406840100072
Figure FPA00001406840100081
Figure FPA00001406840100091
Figure FPA00001406840100101
Figure FPA00001406840100111
Figure FPA00001406840100121
Figure FPA00001406840100131
14. organic electronic devices, it contains first electrode, second electrode, and one or more organic material layers that place between described first electrode and described second electrode, one or more layers in the wherein said organic material layer comprises among the claim 1-13 each compound.
15. the organic electronic devices of claim 14, wherein said organic material layer comprise that electronics injects or transport layer, described electronics injects or transport layer comprises above-claimed cpd.
16. the organic electronic devices of claim 14, wherein said organic material layer comprises luminescent layer, and described luminescent layer comprises above-claimed cpd.
17. the organic electronic devices of claim 14, wherein said organic material layer comprise hole injection or transport layer, described hole is injected or transport layer comprises above-claimed cpd.
18. the organic electronic devices of claim 14, wherein said organic electronic devices are selected from Organic Light Emitting Diode, organophosphorus optical device, organic solar batteries, organic photoconductor (OPC) and organic transistor.
CN201080005081.4A 2009-01-20 2010-01-20 New cycloalkene derivative and use its organic electronic devices Active CN102292324B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR10-2009-0004600 2009-01-20
KR20090004600 2009-01-20
PCT/KR2010/000369 WO2010085087A2 (en) 2009-01-20 2010-01-20 Novel cycloalkene derivatives and organic electronic devices using the same

Publications (2)

Publication Number Publication Date
CN102292324A true CN102292324A (en) 2011-12-21
CN102292324B CN102292324B (en) 2015-11-25

Family

ID=42356321

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201080005081.4A Active CN102292324B (en) 2009-01-20 2010-01-20 New cycloalkene derivative and use its organic electronic devices

Country Status (6)

Country Link
US (1) US9150536B2 (en)
EP (1) EP2390249B1 (en)
JP (1) JP5575806B2 (en)
KR (1) KR101153095B1 (en)
CN (1) CN102292324B (en)
WO (1) WO2010085087A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010137285A1 (en) 2009-05-29 2010-12-02 出光興産株式会社 Anthracene derivative and organic electroluminescent element using the same
KR101358784B1 (en) * 2012-02-14 2014-02-10 삼성디스플레이 주식회사 Organic light-emitting device having improved efficiency characterisitics and organic light-emitting display apparatus including the same
US9312500B2 (en) 2012-08-31 2016-04-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
CN110003199B (en) 2012-09-12 2022-09-23 出光兴产株式会社 Novel compound, material for organic electroluminescent element, and electronic device
CN104640848B (en) 2013-03-15 2018-01-26 出光兴产株式会社 Anthracene derivative and organic electroluminescent element using same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008013399A1 (en) * 2006-07-26 2008-01-31 Lg Chem, Ltd. Anthracene derivatives, organic electronic devices using anthracene derivatives, and electronic apparatuses comprising organic electronic device
CN101238194A (en) * 2005-10-21 2008-08-06 Lg化学株式会社 Indene derivatives and organic light emitting diode using the same
CN101305071A (en) * 2005-11-07 2008-11-12 Lg化学株式会社 Organic electroluminescent device and method for preparing the same

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2246417C (en) 1996-11-22 2009-09-08 Boulder Scientific Company Preparation of chiral titanocenes
EP1786886B1 (en) 2004-09-02 2011-02-23 LG Chem, Ltd. Anthracene derivatives and organic light emitting device using the same as a light emitting material
JP4790260B2 (en) * 2004-12-22 2011-10-12 出光興産株式会社 Organic electroluminescence device using anthracene derivative
JP5089947B2 (en) 2005-09-23 2012-12-05 三星モバイルディスプレイ株式會社 ORGANIC LIGHT-EMITTING COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE HAVING THE SAME
KR100770406B1 (en) 2006-02-27 2007-10-26 네오뷰코오롱 주식회사 Blue luminescent organic compound and organic light-emitting diode including the same
TWI348463B (en) 2006-03-06 2011-09-11 Lg Chemical Ltd Novel anthracene derivative and organic electronic device using the same
KR100852118B1 (en) 2007-03-13 2008-08-13 삼성에스디아이 주식회사 An imidazopyrimidine-based compound and an organic light emitting diode employing an organic layer comprising the same
JP5715336B2 (en) 2007-06-20 2015-05-07 出光興産株式会社 Polycyclic ring assembly compound and organic electroluminescence device using the same
JP2009033114A (en) 2007-06-29 2009-02-12 Tdk Corp Electronic module and method of manufacturing electronic module
KR100910150B1 (en) 2008-04-02 2009-08-03 (주)그라쎌 Novel organic electroluminescent compounds and organic electroluminescent device using the same
EP2256176A1 (en) 2008-06-25 2010-12-01 Gracel Display Inc. Novel organic electroluminescent compounds and organic electroluminescent device using the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101238194A (en) * 2005-10-21 2008-08-06 Lg化学株式会社 Indene derivatives and organic light emitting diode using the same
CN101305071A (en) * 2005-11-07 2008-11-12 Lg化学株式会社 Organic electroluminescent device and method for preparing the same
WO2008013399A1 (en) * 2006-07-26 2008-01-31 Lg Chem, Ltd. Anthracene derivatives, organic electronic devices using anthracene derivatives, and electronic apparatuses comprising organic electronic device

Also Published As

Publication number Publication date
KR20100108505A (en) 2010-10-07
JP5575806B2 (en) 2014-08-20
CN102292324B (en) 2015-11-25
WO2010085087A3 (en) 2010-12-02
US9150536B2 (en) 2015-10-06
JP2012515772A (en) 2012-07-12
EP2390249A2 (en) 2011-11-30
KR101153095B1 (en) 2012-06-04
EP2390249B1 (en) 2015-08-26
US20120037892A1 (en) 2012-02-16
EP2390249A4 (en) 2012-06-27
WO2010085087A2 (en) 2010-07-29

Similar Documents

Publication Publication Date Title
CN101090893B (en) New imidazole derivatives, preparation method thereof and organic electronic device using the same
US8137823B2 (en) Anthracene derivatives, process for preparation thereof, and organic electronic light emitting device using the same
CN101426760B (en) Novel anthracene derivatives, method for preparation thereof, and organic electronic device using the same
CN101896574B (en) New compound and organic light emitting device using the same
KR100867526B1 (en) New diamine derivatives, preparation method thereof and organic electronic device using the same
US11411186B2 (en) Boron heterocyclic compound, display panel and display apparatus
CN104487432A (en) Heterocyclic compound and organic electronic element containing same
JP2014523875A (en) Novel compound and organic electronic device using the same
KR101989952B1 (en) Novel acridine derivatives and organic electroluminescent devices containing them
JP2012530696A (en) Acridine derivatives and organic electroluminescent devices containing the same
CN105431423A (en) Heterocyclic compound and organic light-emitting device comprising same
CN103403125A (en) Novel compound and organic light-emitting device comprising same
WO2001023496A1 (en) Organic electroluminescent element
CN101668730A (en) New diamine derivatives and organic electronic device using the same
JP5276097B2 (en) Organometallic complex derivative and organic light emitting device using the same
CN1863891B (en) Organic compound and organic light emitting device using the same
CN110054644A (en) Compound, display panel and display device
CN110078755A (en) Compound, display panel and display device
JP5650654B2 (en) Novel chrysene derivative and organic electronic device using the same
CN102292324B (en) New cycloalkene derivative and use its organic electronic devices
CN110218212B (en) Nitrogen heterocyclic compound, display panel and display device
JP3642606B2 (en) Organic EL device
KR20120128386A (en) Organic compounds for organic electro luminescente device and organic electro luminescent device using same
KR20110131155A (en) New dithienopyrrole derivatives and organic electronic diode using the same
KR20100045311A (en) New dithienopyrrole derivatives and organic electronic diode using the same

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant